73875-18-0

Basic information

• Product Name: (2′E)-2-(3′-methyl-4′-phenylsulfonylbut-2′-enyl)-1,4-dimethoxy-3-methylnaphthalene
• Synonyms: (2′E)-2-(3′-methyl-4′-phenylsulfonylbut-2′-enyl)-1,4-dimethoxy-3-methylnaphthalene
• CAS NO: 73875-18-0
• Molecular Weight: 410.534
• Mol File: 73875-18-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2′E)-2-(3′-methyl-4′-phenylsulfonylbut-2′-enyl)-1,4-dimethoxy-3-methylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: (2′E)-2-(3′-methyl-4′-phenylsulfonylbut-2′-enyl)-1,4-dimethoxy-3-methylnaphthalene(73875-18-0)
• EPA Substance Registry System: (2′E)-2-(3′-methyl-4′-phenylsulfonylbut-2′-enyl)-1,4-dimethoxy-3-methylnaphthalene(73875-18-0)

Safety Data

• Hazardous Substances Data: 73875-18-0(Hazardous Substances Data)

Upstream product

• 78-79-5 isoprene 
• 98-09-9 benzenesulfonyl chloride 
• 53772-19-3 1,4-dimethoxy-2-methylnaphthalene 
• 59277-17-7 1-(benzenesulfonyl)-2-methyl-4-chloro-2-butene 
• 53772-33-1 2-bromo-3-methyl-1,4-dimethoxynaphthalene 
• 53588-16-2 (E)-4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene 
• 5829-79-8 (E)-4-chloro-2-methyl-1-phenylsulfonyl-2-butene 

Downstream Products

• 1597486-93-5 2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-4-(phenylsulfonyl)octacosa-2,6,10,14,18,22,26-heptaen-1-yl)-1,4-dimethoxy-3-methylnaphthalene 
• 2124-57-4 menaquinone-7 
• 84-81-1 farnoquinone 
• 863-61-6 menatetrenone 
• 618457-08-2 (2'E,6'E,10'E,14'E)-2-(4'-phenylsulfonyl-3',7',11',15'-tetramethylhexadeca-2',6',10',14'-tetraenyl)-1,4-dimethoxy-3-methylnaphthalene 

Relevant articles and documents

Synergistic factors ensue high expediency in the synthesis of menaquinone [K2] analogue MK-6: Application to access an efficient one-pot protocol to MK-9

Here we report a practical and efficient method for the synthesis of menaquinone vitamin (K2) analog MK-6 in all trans forms through “1 + 5 convergent synthetic approach” of pentaprenyl chloride with monoprenyl menadione derivative. In the synergistic factors, less efficient leaving group/more efficient nucleophile (Cl) in the substrate makes it more prominent reaction by eliminating all Sn2’ side reaction products. Further, the addition of acetic acid in the last step (desulfonation) of reaction sequence removes the limitations of the reactions in terms of cyclized side product (multiple reactions of pentaprenyl alcohol with Et3B), byproduct (Et3B, incendiary compound) formations and their interruption in the tricky purification processes. The utility of this method was further extended to find an efficient one-pot synthesis to MK-9 to the gram scale synthesis. This approach is economical and efficient and avoids the awkward chromatographic separation processes.

Convergent synthesis of menaquinone-7 (MK-7)

A practical synthesis of menaquinone-7 (MK-7, vitamin K2) in the all-Trans form was designed. Stereoselective synthesis of MK-7 was achieved through a "1 + 6" convergent strategy by condensation of two building blocks, menadione monoprenyl derivative (fragment "1") with hexaprenyl bromide (fragment "6", 82%). Pd-catalyzed desulfonation with LiEt3BH (78%) was followed by oxidation of the hydroquinone moiety using ammonium cerium(IV) nitrate (72%). The major challenge in our methodology was the preparation of all-Trans hexaprenyl bromide by coupling of two triprenyl units derived from trans,trans-farnesol. Manufacturing on a pilot scale was accomplished through our approach. The scalable method was designed especially for a large, kilogram-scale production from easily available intermediates. Furthermore, the proposed methodology avoids many chromatographic purifications and allows for a relatively cost-effective manufacturing. Moreover, our synthesis yielded high-purity (99.9%) final product MK-7, which can be used as a dietary supplement as well as an active pharmaceutical ingredient.

A New Efficient Method for the Preparation of Sulfone-Functionalized Prenylhydroquinones

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